Tag: M.W=200-300

328-87-0, name is 2-Chloro-5-trifluoromethylbenzonitrile, belongs to nitriles-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 328-87-0

EXAMPLE 7 Preparation of 2-Cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether A solution of potassium hydroxide (2.6 g., 0.04 mole) 87.3% pure and 3-ethoxy-4-nitrophenol (7.3 g., 0.04 mole) in methanol (30 ml) is stripped to dryness under reduce pressure. A residue of potassium 3-ethoxy-4-nitrophenoxide is dissolved in sulfolane (200 g.) and 4-chloro-3-cyano-benzotrifluoride (8.2 g., 0.04 mole) is added. Gas-liquid chromotography shows the reaction to be complete after stirring at 110 C. for 41/2 hours and 135 C for 21/2 hours. The reaction mixture is cooled and poured into deionized water and the precipitate which forms is filtered off and air dried. Recrystallization from isopropanol yields 2-cyano-alpha,alpha,alpha-trifluoro-p-tolyl-3-ethoxy-4-nitrophenyl ether (7.4 g. 53%) m.p. 143-145 C.

The synthetic route of 328-87-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Rohm and Haas Company; US4063929; (1977); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 36282-26-5, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 36282-26-5 as follows.

A mixture of 4-fluoro-2-bromobenzonitrile (10.0 g, 50.0 mmol), potassium acetate (9.82 g, 100 MMOL), bis (pinacolato) diboron (14.0 g, 55.0 mmol) and dichloro [L, L’-BIS (diphenylphosphino) FERROCENE] PALLADIUM (II) CH2CL2 adduct (0.82 g, 1.0 mmol) in 1,4-dioxane (150 ml) and dimethylsulfoxide (3 ml) was degassed with nitrogen for 1 h then heated at 85C for 20 h. The reaction was cooled to ambient temperature and then concentrated in vacuo. The residue was stirred with 2 N sodium hydroxide (250 ml) for 10 min then filtered. The filtrate was extracted with diethyl ether (300 ml) and the organics discarded. The aqueous component was cooled to 0C then treated with 5 N hydrochloric acid, added dropwise over 15 min until the pH was 8. The aqueous phase was extracted with EtOAc (2 x 200 ML), THE COMBINED organics were dried over anhydrous sodium sulfate, filtered and evaporated to afford the title compound (10.9 g, 88%) as a pale brown solid: BA (360 MHz, CDCL3) 1.38 (12 H, s), 7.15-7. 25 (1 H, M), 7.53-7. 60 (1 H, m), 7.67-7. 75 (1 H, m).

According to the analysis of related databases, 36282-26-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Related Products of 114897-91-5,Some common heterocyclic compound, 114897-91-5, name is 2-(4-Bromo-2-fluorophenyl)acetonitrile, molecular formula is C8H5BrFN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of Mel (3.2 mL, 49.3 mmol) in anhydrous DMF (82 mL) at 0 C. was added NaH (60%, 2.0 g), followed by (4-bromo-2-fluorophenyl)acetonitrile (3.5 g, 16.4 mmol). The mixture was slowly warmed up to room temperature and stirred for 3 hours. The reaction was quenched by the addition of saturated NH4Cl and extracted with EtOAc (3×150 mL). The combined organic extracts were washed with brine, dried with Na2SO4 and evaporated to dryness. The mixture was purified by flash column chromatography (0-20% EtOAc in hexanes) to give the product (3.0 g, 77% yield). 1H NMR (300 MHz, CDCl3) delta: 1.78 (s, 6H), 7.26-7.42 (m, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromo-2-fluorophenyl)acetonitrile, its application will become more common.

Reference:
Patent; Agouron Pharmaceuticals, Inc.; US2005/176701; (2005); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Reference of 425379-16-4, These common heterocyclic compound, 425379-16-4, name is 2-Bromo-3-fluorobenzonitrile, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

The product of Example 12 step a) (1.00 g, 4.57 mmol) and 2-BROMO- 3-FLUOROBENZONITRILE (0.91 g, 4.57 mmol) were suspended in 1, 2- dimethoxyethane (20 ml) and 2 N sodium carbonate (10 ml) and the mixture degassed with nitrogen for 30 min. TETRAKIS-TRIPHENYLPHOSPHINE palladium (0) (211 mg, 0.18 mmol) was added and the mixture was heated at 80C for 18 h. The mixture was allowed to cool to ambient temperature, DILUTED WITH ETHYL ACETATE (100 ML) AND WASHED WITH 2 N SODIUM HYDROXIDE solution (75 ml), water (50 ml) and brine (50 ml), dried over anhydrous sodium sulfate, filtered and evaporated to give a pale yellow oil. The oil was purified by flash column chromatography on silica eluting with 0-15% ETOAC/ISOHEXANE to give 0.39 g (29%) of the title compound as a colourless oil which solidified on standing: ON (400 MHz, CDCL3) 7.19 (1 H, ddd, J 8.0, 8.0, 1.0), 7.34-7. 38 (1 H, m), 7.44 (1 H, td, J9.0, 1.4), 7.50-7. 56 (1 H, m), 7.61 (1 H, ddd, J7. 8, 1.0, 0.6), 7. 68-7. 72 (1 H, m).

The synthetic route of 425379-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME LIMITED; WO2004/65388; (2004); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 179897-89-3, name is 5-Bromo-2-fluorobenzonitrile, A new synthetic method of this compound is introduced below., Application In Synthesis of 5-Bromo-2-fluorobenzonitrile

(1) 5-bromo-2-fluoro-1-cyanobenzene (II, 3 g, 15 mmol) under N2 protection,Sodium sulfide (1.3 g, 16.5 mmol) was reacted in DMF (30 mL) at room temperature for 5 h.Add 300 mL of sodium hydroxide solution (1 mol/L) and stir for 0.5 h.Wash with dichloromethane (300 mL × 2), acid phase with hydrochloric acid (6 mol / L) to pH = 2, dichloromethane (400 mL × 2),The combined organic layers were washed with brine, dried over anhydrous magnesium5-bromo-2-thio-1-cyanobenzene (III)1.0 g, yield 31.2%.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; South China University of Technology; Li Jing; Li Xiaolei; Zhou Haiyan; Wu Fangping; Zhang Lei; (12 pag.)CN108218777; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 950596-58-4, name is 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows., category: nitriles-buliding-blocks

(12.2 g, 50 mmol) (E)-N,N’-bis(3-ethynylphenyl)methyl ether (Compound B) and (13.3 g, 50 mmol) 2-Amino-4,5-bis(2-methoxyethoxy)benzonitrile (Compound C3), 0.5 g of p-toluenesulfonic acid was added to 50 mL of toluene,After heating to 110 C in an oil bath for 5 h, after TLC monitoring reaction, after cooling to room temperature, concentrated, add ice water and stir for 1 h.The brown solid product erlotinib 17.34 g was obtained in a yield of 88.2%, HPLC: 99.24%.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 950596-58-4.

Reference:
Patent; Yancheng Normal College; Nanjing University Of Technology Dafeng Ocean Industrial Institute; Sun Yaquan; Chen Zhiyuan; Gu Huiwen; Zhang Lijie; Yang Kang; Zong Chaoyang; (11 pag.)CN108503596; (2018); A;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Application of 154607-01-9,Some common heterocyclic compound, 154607-01-9, name is 4-Bromo-2-chlorobenzonitrile, molecular formula is C7H3BrClN, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

1-(Benzo[d][1,3]dioxol-5-yl)-N-(4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)cyclopropanecarboxamide (0.084 g, 0.20 mmol), 4-bromo-2-chlorobenzonitrile (0.043 g, 0.20 mmol), aqueous potassium carbonate (520 muL, 1M), FibreCat 1007 (7 mg), and DMF (1 mL) were combined. The mixture was heated at 80 C. for 18 hours. After cooling, the mixture was filtered and purified by preparative HPLC to provide 1-(benzo[d][1,3]dioxol-5-yl)-N-(3′-chloro-4′-cyano-6-methylbiphenyl-3-yl)cyclopropanecarboxamide.

The synthetic route of 154607-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Vertex Pharmaceuticals Incorporated; Van Goor, Fredrick F.; Burton, William Lawrence; US2015/231142; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 79463-77-7, The chemical industry reduces the impact on the environment during synthesis 79463-77-7, name is Diphenyl N-cyanocarbonimidate, I believe this compound will play a more active role in future production and life.

Diphenyl N-cyanocarbonimidate [79463-77-7] (200 mg, 0.81 mmol) and 3,4-dimethoxyaniline [6315- 89-5] (137 mg, 0.89 mmol) were dissolved in DCM (2 mL) and 2-propanol (2 mL) and DIPEA (159 mg, 1.22 mmol) were added and the reaction mixture was stirred at r.t. for ~1 h. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica (gradient elution with 15 – 100% EtOAc/hexane) to afford the title compound (198 mg, 82%) as a white solid. dH (300 MHz, DMSO -d6) 10.65 (s, 1H), 7.51 – 7.37 (m, 2H), 7.36 – 7.22 (m, 3H), 7.09 (d, J 1.8 Hz, 1H), 7.03 – 6.91 (m, 2H), 3.75 (s, 6H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Diphenyl N-cyanocarbonimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UCB BIOPHARMA SRL; CHOVATIA, Prafulkumar Tulshibhai; CONNELLY, Rickki Lee; FRANKLIN, Richard Jeremy; HASLETT, Gregory William; HENRY, Alistair James; MADDEN, James; NEUSS, Judi Charlotte; NORMAN, Timothy John; PHILPS, Oliver; PITT, William Ross; RAMPALAKOS, Konstantinos; SELBY, Matthew Duncan; SELVARATNAM, Suganthan; TRANI, Giancarlo; ZHU, Zhaoning; (768 pag.)WO2019/243550; (2019); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 4592-94-3, name is 3-(4-Bromophenyl)-3-oxopropanenitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 4592-94-3, Safety of 3-(4-Bromophenyl)-3-oxopropanenitrile

General procedure: A mixture of 1,2-bis(bromomethyl)benzene (1.0 mmol), alpha-cyanoacetophenone (1.0 mmol) and Cs2CO3 (3.0 mmol) in DMSO (5 mL) was stirred at 80 C for 4 h till almost full conversion of the substrates by TLC analysis. The resulting mixture was dropped into 100 mL 1 M HCl (aq) and extracted with EtOAc three times (3×50 mL). The organic extract was dried with Na2SO4, filtered and concentrated. The crude product was purified by column chromatography on silica gel (eluent: petroleum ether/EtOAc=50/1) to afford the product 3aa as a white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Wang, Jungang; Xiang, Jiachen; Wang, Miao; Guan, Jie; Wu, Anxin; Tetrahedron; vol. 70; 7; (2014); p. 1412 – 1417;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Adding a certain compound to certain chemical reactions, such as: 144649-99-0, name is 5-Bromo-2-methoxybenzonitrile, belongs to nitriles-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 144649-99-0, name: 5-Bromo-2-methoxybenzonitrile

Preparation of Intermediate 1-2; 5-(2-Chloropyrimidin-4-yl)-2-methoxybenzonitrileReagents: (a) Pd(dppf)Cl2, KOAc, /?-dioxane: (b) 2,4-dichloropyrimidine, K2C03,Pd(PPh3)4, CH3CN, H20, reflux, 5 h;[0209] Step 1. 2-Methoxy-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzonitrile: To a solution of 2-methoxy-5-bromobenzonitrile (5.0 g, 23.6 mmol) in /?-dioxane (125 mL), bis(pinacolato)diborane (9.0 g, 35.4 mmol), KOAc (7.0 g, 71.3 mmol), and Pd(dppf)Cl2 (0.863 g, 1.17 mmol) were added. The resulting mixture was stirred for 18 h at 80 C. The cooled reaction crude was diluted with 120 mL EtOAc, washed with H20 and brine, dried (Na2S04), filtered, and concentrated in vacuo. The residue was purified by column chromatography on Si02 (Hexanes/EtOAc) to afford the title compound (5.6 g, 92%). GC/MS (EI, M+) 245

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-methoxybenzonitrile, and friends who are interested can also refer to it.

Reference:
Patent; MYREXIS, INC.; HOLCOMB, Ryan C.; SEBAHAR, Paul R.; SUZUKI, Kazuyuki; McLEOD, Donald A.; DASTRUP, David M.; HOARAU, Christophe; HALTER, Robert J.; BURSAVICH, Matthew Gregory; SHENDEROVICH, Mark D.; RICHARDS, Burt; BARTEL, Paul L.; WO2012/142329; (2012); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts